Methyl Salicylate → HCID 1729098, compound

HRID 660784Notes

Reaction equation

HRID 660784 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH3:12][S:13](Cl)(=[O:15])=[O:14]>N1C=CC=CC=1>[CH3:11][O:10][C:1](=[O:9])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][S:13]([CH3:12])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 4133Methyl SalicylateHCID 31297Methanesulfonyl chloride

Product 1

HCID 1729098HCID 1729098, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl salicylate (3.04 g, 20 mmol) in pyridine (25 mL) is added dropwise methanesulfonyl chloride (2.17 g, 19 mmol) and the mixture is stirred at RT for 18 h. The solvent is removed under reduced pressure and the residue partitioned between EtOAc and water. The organic phase is washed sequentially with 1N HCl, 2N Na2CO3, 1N HCl, water and brine then is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue purified by column chromatography using a gradient of 0-100% EtOAc/hexane as eluent to give the title compound as a solid.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue partitioned between EtOAc and water
  3. washThe organic phase is washed sequentially with 1N HCl, 2N Na2CO3, 1N HCl, water and brine
  4. dry with materialthen is dried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-378911f26dc2470584f38ca0b2abc115
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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